After making just two movies — "The Station Agent" and "The Visitor" — writer-director Tom McCarthy already had established himself as a filmmaker with a real knack for creating beautifully fleshed-out characters, full of humor and believable flaws.
He continues to impress with "Win Win," and once again amasses an excellent cast; a longtime supporting player himself, McCarthy always brings out the best in his character actors.
Paul Giamatti stars as Mike Flaherty, a small-town New Jersey attorney who agrees to take on the guardianship of an elderly client (Burt Young) who's starting to suffer from dementia. Mike thinks he's got a good little deal going: Instead of caring for the old man on a daily basis, he sticks him in a nursing home and pockets the $1508 stipend every month. It's a win-win, he figures. His wife, Jackie (Amy Ryan), and two young daughters could use the money, and the client gets better care this way. It's not that much cash, so it's not like he's really stealing.
What Mike doesn't count on is the arrival of Kyle (Alex Shaffer in his film debut), the client's wayward grandson. He's got plenty of cigarettes, hair product and attitude, but he's got nowhere else to go, so Mike and Jackie agree to take him in. Mike just happens to be a part-time high school wrestling coach, and Kyle just happens to be a part-time high school wrestler — and once he opens up, he turns out to be a nice guy to boot. Whaddya know? Another win-win.
But you can imagine the unraveling happening before it even starts. There's no way these convenient arrangements can last long. And that's before Kyle's mother (Melanie Lynskey) shows up, fresh out of rehab, with some plans of her own — and a lawyer in tow (the ever reliable Margo Martindale).
Still, McCarthy never judges Mike, but rather allows him to enjoy one small victory after another, and make one mistake after another. Mike's best friend and assistant coach, Terry (Bobby Cannavale, who also starred in "The Station Agent"), can't bring himself to disapprove, because the kid's a stud athlete and winning feels so good. No matter that Kyle's a bit of a cipher; that's actually the point, that these middle-aged men can project all their hopes and dreams onto him and live vicariously through him. (The always-great Jeffrey Tambor co-stars as Mike's office mate and fellow coach, and while he, Giamatti and Cannavale bounce off each other perfectly in their passive-aggressive game of one-upmanship, he doesn't get nearly enough screen time; Tambor actually disappears about halfway through without much explanation.)
"Win Win" teeters on the brink of sports-movie feel-goodery — complete with a training montage — but McCarthy's too clever, and too attuned to realism, to rely on formula. Instead, he's more interested in exploring the choices people make, and the way they justify their actions.
Giamatti, as always, conveys every facet of his character's complexity, with those bug eyes, hunched carriage and constant sense of exasperation. His sad-sack demeanor alone makes you want to root for him to succeed, even though you know he can't — and shouldn't. McCarthy doesn't place him in deadly serious situations, only mildly and temporarily difficult ones, but still manages to wring those for warm laughs.
There's no great narrative momentum to "Win Win," and that's fine, because it's such an enjoyable little slice of life.